Ligands for copper-catalyzed C-N bond forming reactions with 1 Mol% CuBr as catalyst

Journal of Organic Chemistry

Volumn 76, Issue 9, 2011, Pages 3151-3159

  Yang, Kai ^a,b   Qiu, Yatao ^a   Li, Zheng ^c   Wang, Zhaoyang ^b   Jiang, Sheng ^a  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

^b SOUTH CHINA NORMAL UNIVERSITY   (China)

^c HOUSTON METHODIST RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINES; ARYL IODIDES; BOND-FORMING REACTIONS; C-N COUPLING; CATALYST LOADINGS; CATALYTIC SYSTEM; CATALYZED COUPLING; CHEMO-SELECTIVITY; N-HETEROCYCLES;

BROMINE COMPOUNDS; CATALYSIS; CATALYSTS; CHLORINE COMPOUNDS; DISPLAY DEVICES; FUNCTIONAL GROUPS;

LIGANDS;

8 HYDROXYQUINOLIN NITROGEN OXIDE; ALIPHATIC AMINE; BROMIDE; CHLORIDE; COPPER; GROUPS WITH A CARBON-NITROGEN BOND ONLY; HETEROCYCLIC NITRO COMPOUND; IODIDE; METHYL PICOLINATE NITROGEN OXIDE; METHYL QUINOLINE 2 CARBOXYLATE NITROGEN OXIDE; PICOLINIC ACID NITROGEN OXIDE; QUINOLINE 2 CARBOXYLIC ACID NITROGEN OXIDE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION;

BROMIDES; CARBON; CATALYSIS; COPPER; LIGANDS; NITROGEN;

EID: 79955564755     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1026035     Document Type: Article

References (76)

1. For recent reviews see: Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359
2. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400
3. Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428
4. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337
5. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
6. Evano, G.; Toumib, M.; Costea, A. Chem. Commun. 2009, 4166
7. Lindley, J. Tetrahedron. 1984, 40, 1433
8. For recent review, see: Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096
9. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954
10. Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581
11. Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703
12. Antila, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578
13. Klapars, A.; Antila, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727
14. Antila, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684
15. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421
16. Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459
17. Cai, Q.; Zhu, W.; Zhang, H.; Zhang, Y.; Ma, D. Synthesis 2005, 496
18. Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164
19. Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453
20. Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583
21. Wang, Z.; Bao, W.; Jiang, Y. Chem. Commun. 2005, 2849
22. Kim, J.; Chang, S. Chem. Commun. 2008, 3052
23. Lu, Z.; Twieg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 6289
24. Lu, Z.; Twieg, R. J. Tetrahedron 2005, 61, 903
25. Zhang, Z.; Mao, J.; Zhu, D.; Wu, F.; Chen, H.; Wan, B. Tetrahedron. 2006, 62, 4435
26. Xu, L.; Mao, J.; Zhu, D.; Wu, F.; Wang, R.; Wan, B. Tetrahedron 2005, 61, 6553
27. Zhu, D.; Xu, L.; Wu, F.; Wan, B. Tetrahedron Lett. 2006, 47, 5781
28. Liang, L.; Li, Z.; Zhou, X. Org. Lett. 2009, 11, 3294
29. Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742
30. de Lange, B.; Lambers-Verstappen, M. H.; Schmieder-van de Vondervoort, L.; Sereinig, N.; de Rijk, R.; de Vries, A. H. M.; de Vries, J. G. Synlett 2006, 3105
31. Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490
32. Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863
33. Xia, N.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 337
34. For other ligands on Cu-catalyzed C-N coupling, see: Gujadhur, R.; Venkataraman, D.; Kintigh, J. T. Tetrahedron Lett. 2001, 42, 4791
35. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793
36. Zhang, Z.; Mao, J.; Zhu, D.; Wu, F.; Chen, H.; Wan, B. Tetrahedron 2006, 62, 4435
37. Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 1994
38. Yang, M.; Liu, F. J. Org. Chem. 2007, 72, 8969
39. Jiang, D.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2007, 72, 672
40. Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2005, 70, 8017
41. Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem.-Eur. J. 2006, 12, 3636
42. Zhu, X.; Ma, Y.; Su, L.; Song, H.; Chen, G.; Liang, D.; Wan, Y. Synthesis 2006, 3955
43. Taillefer, M.; Xia, N.; Ouali, A. Angew. Chem., Int. Ed. 2007, 46, 934
44. Mao, J.; Guo, J.; Song, H.; Ji, S. Tetrahedron 2008, 64, 1383
45. Wang, H.; Li, Y.; Sun, F.; Feng, Y.; Jin, K.; Wang, X. J. Org. Chem. 2008, 73, 8639
46. Suresh, P.; Pitchumani, K. J. Org. Chem. 2008, 73, 9121
47. Jones, K. L.; Porzelle, A.; Hall, A.; Woodrow, M. D.; Tomkinson, N. C. O. Org. Lett. 2008, 10, 797
48. Ntaganda, R.; Dhudshia, B.; Macdonald, C. L. B.; Thadani, A. N. Chem. Commun. 2008, 6200
49. Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Chem.-Eur. J. 2004, 10, 5607
50. Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695
51. Jiang, Q.; Jiang, D.; Jiang, Y.; Fu, H.; Zhao, Y. Synlett 2007, 1836
52. Ma, H.-C.; Jiang, X.-Z. J. Org. Chem. 2007, 72, 8943
53. Wang, D.; Ding, K. Chem. Commun. 2009, 1891
54. Zhu, L.; Li, G.; Luo, L.; Guo, P.; Lan, J.; You, J. J. Org. Chem. 2009, 74, 2200
55. Yang, C.-T.; Fu, Y.; Huang, Y.-B.; Yi, J.; Guo, Q.-X.; Liu, L. Angew. Chem., Int. Ed. 2009, 48, 7398
56. Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120
57. Tye, J. W.; Weng, Z.; Johns, A. M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 9971
58. Kaddouri, H.; Vicente, V.; Ouali, A.; Ouazzani, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 333
59. Xie, Y.-X.; Pi, S.-F.; Wang, J.; Yin, D.-L.; Li, J.-H. J. Org. Chem. 2006, 71, 8324
60. Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120
61. Tye, J. W.; Weng, Z.; Johns, A. M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 9971
62. Hong, S.; Gupta, A. K.; Tolman, W. B. Inorg. Chem. 2009, 48, 6323
63. Yamamoto, Y.; Miura, A.; Kawamata, A.; Miura, M.; Takei, S. Bull. Chem. Soc. Jpn. 1978, 51, 3489
64. Prasad, M. R.; Kamalakar, G.; Madhavi, S.; Kulkarni, S. J.; Raghavan, K. V. Chem. Commun. 2000, 1577
65. Hamana, M.; Noda, H. Chem. Pharm. Bull. 1970, 18, 26
66. Tolstikov, G. A. J. Org. Chem. USSR (Engl. Translation) 1972, 8, 1200
67. Okano, K.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2003, 5, 4987
68. Lu, Z.; Twieg, R. J. Tetrahedron Lett. 2005, 46, 2997
69. Guillon, J.; Dallemagne, P.; Pfeiffer, B.; Renard, P.; Manechez, D.; Kervrand, A.; Raulv., S. Eur. J. Med. Chem. 1998, 33, 293
70. Liu, L.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider, P. J. J. Org. Chem. 2005, 70, 10135
71. Sreedhar, B.; Arundhathi, R.; Reddy, P. L.; Kantam, M. L. J. Org. Chem. 2009, 74, 7951
72. Zhu, X.; Su, L.; Huang, L.; Chen, G.; Wang, J.; Song, H.; Wan, Y. Eur. J. Org. Chem. 2009, 5, 635
73. Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490
74. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793
75. Lee, H.-G.; Won, J.-E.; Kim, M.-J.; Park, S.-E.; Jung, K.-J.; Bo, R. K.; Lee, S.-G.; Yoon, Y.-J. J. Org. Chem. 2009, 74, 5675
76. Butler, K. Perkin Trans. 1 1975, 61